This paper introduces JiraiBench, the first bilingual benchmark for evaluating large language models' effectiveness in detecting self-destructive content across Chinese and Japanese social media communities. Focusing on the transnational "Jirai" (landmine) online subculture that encompasses multiple forms of self-destructive behaviors including drug overdose, eating disorders, and self-harm, we present a comprehensive evaluation framework incorporating both linguistic and cultural dimensions. Our dataset comprises 10,419 Chinese posts and 5,000 Japanese posts with multidimensional annotation along three behavioral categories, achieving substantial inter-annotator agreement. Experimental evaluations across four state-of-the-art models reveal significant performance variations based on instructional language, with Japanese prompts unexpectedly outperforming Chinese prompts when processing Chinese content. This emergent cross-cultural transfer suggests that cultural proximity can sometimes outweigh linguistic similarity in detection tasks. Cross-lingual transfer experiments with fine-tuned models further demonstrate the potential for knowledge transfer between these language systems without explicit target language training. These findings highlight the need for culturally-informed approaches to multilingual content moderation and provide empirical evidence for the importance of cultural context in developing more effective detection systems for vulnerable online communities.